Silly Rappers Talking Silly (Part 1 of 3)by Miles Marshall Lewis

Prince produced, arranged, composed and performed nine studio albums before contending with hiphop. The song, the live recording “It’s Gonna Be a Beautiful Night,” stretches all the way back to 19th century English poet Edward Lear for Sheila E.’s rhythmic reading of the 1871 poem, “The Table and the Chair.” A lot led up to that moment. Prince had gained, lost, gained back and lost again his core African-American audience. Rap music was just overcoming the perception of its earliest days as a fad, selling into the multimillions. (At that moment, 1987, Prince could not outsell Run-DMC.) A sea change was afoot. And so Prince finally applied his notorious art of seduction to hiphop. It did not go well.

Prince was born in the American heartland of Minneapolis, Minnesota, on June 7, 1958, the son of jazz pianist John Lewis Nelson and his second wife, singer Mattie Della Shaw. Père Nelson made ends meet as a plastic molder at Honeywell Electronics and named his son after his band, the Prince Rogers Trio. Young Prince learned the theme to Batman on his father’s piano, put in his 10,000 hours of mastery, and moved on to the guitar. Then bass. Then drums. By high school he’d joined his own band, Grand Central, which led to another band, Shampayne, which led to a three-album deal with Warner Bros. Records at 19.

“Don’t make me Black,” he told Warner Bros. president Larry Waronker the day he signed his name on the dotted line. “My idols are all over the place.” Three years later Prince and a multiracial backing band were performing “I Wanna Be Your Lover” and shaking hands with Dick Clark on American Bandstand, not Don Cornelius on Soul Train.

The racial pendulum swing of Prince’s audience went something like this.

For You, his April 1978 debut, peaked at 21 on the Black albums chart and 163 on the pop chart. Prince, released the following October, reached all the way up to number three on the Black chart and 22 on the pop chart. As segregated as American radio and marketing departments could be, Prince still scanned as a rhythm and blues artist with heavy potential to cross over to pop-rock radio. (Prince’s “I Wanna Be Your Lover,” his first number one R&B hit, made it to number 11 on the pop singles chart.)

Dirty Mind was different. With new wave sonics and rockabilly tendencies, Prince sang of getting head and sexing his own sister, and a punk-funk raconteur was born. This one Rolling Stone took notice of, judging it “the most generous album about sex ever made by a man.” To say Prince first lost his Black audience with Dirty Mind of course simplifies the matter. The record still did better on the Black chart. But his bid for a rock audience was clear, his aim to meld both followings understood. Prince campaigned as an erotic politician more in the vein of Mick Jagger than Marvin Gaye, and he was winning.

As left of center as Dirty Mind may have been—Prince prancing onstage in bikini briefs and high-heel boots underneath a flasher’s trench coat—the following year’s Controversy moved more to the R&B middle. A great record on its own (see the synthezoid funk of “Controversy” (“I wish there was no Black and white/I wish there were no rules”) and “Do Me, Baby,” his most seductive ballad to date), the truly revealing chess play of 1981 was the release of the premiere album of The Time. Led by Morris Day, Prince’s drummer from his old high school band Grand Central, The Time fulfilled Prince’s vision of the quintessential R&B band. Prince wrote every word on The Time and played every instrument, while busy uniting “white, Black, Puerto Rican, everybody just a-freakin’ ” uptown on his own records. He’d solved the racial schism: pursuing crossover mega-success in his own career while still satisfying his core Black audience with uncut funk through The Time. His solution worked only too well. While Prince was pelted with garbage opening for the Rolling Stones in ’81, The Time outsold Controversy.

A maelstrom of sexiness, attitude, expertly programmed Linn LM-1 beats, jaunty Oberheim synth chords and ambitious payback made 1999 the party record of the decade. To know it is to love it: “1999,” “Delirious,” “Little Red Corvette.” “Automatic,” “Lady Cab Driver,” “International Lover.” On “D.M.S.R.” (over eight minutes of sinewy bass, new wave keyboards and commanding confidence) Prince exhorts “all the white people in the house”—along with Japanese, Puerto Ricans and “Negroes”—to chant “dance, music, sex, romance.” Once MTV (newly launched in August ’81) put Prince into heavy rotation, his concerts started reflecting that multiracial worldview more and more. The Time’s sophomore set What Time Is It? would not outsell 1999.

By 1984 and Purple Rain, the first appearance of rap on a Prince record is only three years out. Where was hiphop at this point? Incubating in the Bronx for years, the breakout hit that put the world on notice—“Rapper’s Delight” by The Sugarhill Gang, of course—dropped the year after Prince’s first album. The quasi-autobiographical Purple Rain made lists as one of 1984’s highest grossing movies ($68 million), and film had also helped spread hiphop by then: 1983’s underground Wild Style and the PBS graffiti documentary Style Wars; 1984’s Beat Street and Breakin’. Hardly standard practice yet, rap verses started appearing at the center of pop and R&B songs like Blondie’s “Rapture” (1980), Teena Marie’s “Square Biz” (1981) and the Chaka Khan cover of Prince’s “I Feel for You” (1984).

But a word about Purple Rain, the movie. Touring for Controversy in 1982, Prince conceived of a documentary concert film slash glam-funk fantasia entitled The Second Coming. This dry run for Purple Rain never got its close-up or even its rough cut. But the concept evolved into the original visual album, one of the greatest films of rock history. Two racial notes bare mention. Greek-Italian actress Olga Karlatos portrayed Prince’s abused mother in the film, feeding a biracial fiction Prince already planted in interviews. And with the addition of Wendy Melvoin on guitar, Prince promoted his 1999 touring band—now The Revolution—to a prominent place in his mythos through the film and its attendant videos: a multiracial funk-rock quintet intentionally in the vein of Sly and the Family Stone. One nation under a groove.

For my money, peak Prince begins at 1999 and ends at 1988’s Lovesexy (ended partially, as addressed in a few paragraphs, because of peak hiphop): six years of straight swish, six years in the zone. Perhaps no one suspected it at the time, but none of Prince’s next 33 studio albums would ever match the commercial success of Purple Rain, would never even come anywhere near selling over 25 million records worldwide. Less than 12 months after Purple Rain—forever his definitive statement to casual music fans—Prince and the Revolution released their second record as a band: the way more insular Around the World in a Day.

This was the first of two Prince-lost-his-Black-audience records (an oversimplification, but hear me out): psychedelic influenced, less than a minute shorter than Purple Rain, full of nine songs like Purple Rain, but from a slightly different world than everything that came before it. He’d never been as emotionally mature or Joni Mitchell moody as on “Condition of the Heart.” Middle Eastern instruments came in: oud, darbuka and finger cymbals on the title track. Also, cello, violin and viola on “Raspberry Beret” and “The Ladder”; sax on “Temptation” and “The Ladder.” Around the World in a Day—the first release on his own Warner Bros.-distributed record label, Paisley Park Records—marked a sonic expansion, and a reversal from appeasing fly-by-night fans who’d just discovered him the previous year. (The Purple Rain tour hadn’t featured songs from any album older than 1999.)

“Raspberry Beret” and “Pop Life” fared pretty equally on Black and white singles charts, top 10 hits that endure in his catalog. But I was a 14-year-old Prince fanatic then, and I remember the drop-off in interest at my mainly Black Bronx high school. Hiphop had just matured as an album format, and Prince’s stiff competition for young Black ears included LL Cool J’s Radio (the debut album on Def Jam Recordings) and Run-DMC’s King of Rock. Prince knew. Because the year 1985 spawned his first rap song: the Sheila E. track, “Holly Rock.”

Live horns made their way into Prince music via the 1984 debut album of drummer Sheila E. Saxophonist Larry Williams’s riffs on “The Glamorous Life” endure on pop radio to this day, the first use of the sax on a Prince-written song. String sections first appeared on “Purple Rain,” “Raspberry Beret” and “The Ladder,” but arranger Clare Fischer began his longstanding relationship with Prince on The Family in 1985. (Singers Paul Peterson and Susannah Melvoin led The Family, a quintet formed to replace The Time, distinguished by Fischer’s string arrangements and the saxophone of Eric Leeds.) The following year, strings were all over Prince’s eighth studio album, Parade. Sonic experiments sometimes appeared on Prince-related offshoot projects before making their way onto his proper albums. Hence, “Holly Rock.”

Sheila E. didn’t have the greatest experience filming Krush Groove, the thinly veiled biopic of Def Jam Recordings co-founder Russell Simmons, hazed by her rapping co-stars on a regular basis. Run-DMC, Kurtis Blow and the Fat Boys commanded lead roles. LL Cool J and Beastie Boys made cameos. Someone somewhere in Hollywood made the curious decision to cast Sheila E. as the love interest instead of, say, the Real Roxanne or Rae Dawn Chong. At some point in the film, Sheila filters hiphop through her own paisley veil (which is Prince’s paisley veil) and performs “Holly Rock.” To say there were guffaws at the Whitestone multiplex theater in the Bronx where I saw the movie wouldn’t be fair. But a collective smirk ran across my posse’s faces; she’d overstepped her boundaries. Her rhyme, something about “a funky little thing called Holly Rock” (not to be confused with Hollyrock, the cartoon Flintstones’ prehistoric Hollywood, “it might be a dance, it might be a song”), wasn’t authentic to rap music. Prince showed up on set the day director Michael Schultz filmed “Holly Rock,” and the audience of Krush Groove extras needed to be instructed to applaud. If “Holly Rock” worked at all, it was because the song didn’t really seem meant to be a rap song. Full of “good God” exhortations, organ and sax stabs from Eddie M., the song—cute for what it was—proved nothing more than that rap was nowhere near as easy to pull off as masters of ceremony Run or DMC made it look. Even for Prince.

Parade came next in the Prince catalog, the 1986 soundtrack to Under the Cherry Moon. The film—a Black-and-white romantic comedy set in the south of France, directed by Prince—flopped hard. Sales fell off further from Around the World in a Day (by half as much, at a million copies sold), and if his Black audience continued to erode, so too, arguably, did his white audience. However. Prince spent his cinematic follow-up to Purple Rain pursuing and falling in love with English actress Kristin Scott Thomas. In real life Prince was engaged for the first time, to Revolution guitarist Wendy Melvoin’s twin, Susannah. If perception is reality, then in straight-from-the-hip, Black barbershop talk: biracial beauties Vanity, Apollonia and Sheila E. were behind him and Prince, musically and otherwise, might have been slipping into a sunken place. Or definitely had already, depending on who in the barbershop you’re talking to.

All of which catches us up to 1987, and the first appearance of hiphop on a Prince album.

“It’s Gonna Be a Beautiful Night” is built on a simple two-four beat, a horn line from Eric Leeds, and the chant of the Winkies from The Wizard of Oz (the melodic mantra “oh-we-oh, ooooh”). For the masterpiece double album that gives birth to the song, Sign o’ the Times, Prince had disbanded The Revolution and gone it alone. The most reasonable explanation seemed to be that he wanted to get back to basics, back to recording solo, without the input and inspiration of Wendy Melvoin and Lisa Coleman (who’d become particularly trusted collaborators) or any of the rest of them. Prince, ever cryptic, never explained. But “It’s Gonna Be a Beautiful Night” features The Revolution anyway, they’d all recorded the nine-minute jam live at Le Zénith arena in Paris during a sound check on the Parade tour in August 1986.

The original jam has no lyrics, just Prince’s throwing out band and audience commands. He recorded overdubs in November, including his own falsetto vocals and a rap by Sheila E. laid over bass player Brown Mark’s solo. Sheila wasn’t present with Prince at Sunset Sound studios in Hollywood; she literally phoned it in from on tour with Lionel Richie. Liner notes call it the “transmississippi rap,” because Prince and Sheila were separated by the Mississippi River.

Sign o’ the Times came in March 1987. I was a 16-year-old bookish B-boy by then. What excited rap lovers like me that year? The hyper-lyricism of Big Daddy Kane’s “Raw” and Rakim’s “I Know You Got Soul,” the SP-12 drum machine pattern on the Audio Two’s “Top Billin’,” the dancehall-tinged rap flow on Boogie Down Productions’ “The Bridge Is Over.” It was a banner year for hiphop’s first golden age: Salt-N-Pepa’s “Tramp” gave women a voice, as did Roxanne Shanté (“Have a Nice Day”) and MC Lyte (“I Cram to Understand U (Sam)”); Biz Markie was effortlessly silly on “Nobody Beats the Biz”; Public Enemy set agitprop Black nationalism rhymes over an atonal saxophone wail for “Rebel Without a Pause.” If you were young and loved rap music, you were feverishly interpreting the intricate rhyme schemas of rhyme schemers Rakim and Big Daddy Kane, not the transmississippi rap.

Ironically enough, hiphop on “It’s Gonna Be a Beautiful Night” is not an earsore. Prince’s strategic placement of Sheila E. rapping a poem from 116 years prior over the telephone, it worked for this song. Prince record buyers didn’t come to his albums to hear hiphop organically integrated into his music. The wholesale integration of hiphop into Black pop was just around the corner—Bobby Brown’s 1988 breakout album Don’t Be Cruel, Teddy Riley’s ubiquitous New Jack Swing production—and the multiple millions of albums sold by Beastie Boys, Run-DMC and the rest said something serious about what people wanted to hear, and how tastes were changing. What “It’s Gonna Be a Beautiful Night” tells us is that Prince knew he had to wrestle with a sound, an aesthetic, that he was already out of step with.

No Sign o’ the Times tour ever travelled to the United States, but 1988’s Lovesexy brought Prince back to American arenas with an elaborately staged live show, and his poetic tour program let us know he had ears in those Black barbershops: “‘No longer daring,’ his enemies said. ‘No longer glam, his funk is half-assed,’ ” he wrote, paraphrasing them. That year, Lovesexy really wasn’t as daring to younger, on-trend African Americans as Public Enemy’s It Takes a Nation of Millions to Hold Us Back or N.W.A’s Straight Outta Compton. Tellingly, the album’s lead single, “Alphabet St.,” featured another inauthentic rap verse by his new scantily clad back-up dancer, Cat Glover. But Lovesexy failed to crack the top 10 or sell even a million copies, Prince’s poorest-selling album in seven years.

Listen to this playlist which includes many of the tracks in this essay:

Miles Marshall Lewis has written for The New York Times, Rolling Stone, Ebony, Essence and many other publications. His work has appeared in Black Cool: One Thousand Streams of Blackness, Hip-Hop: A Cultural Odyssey, The Believer Book of Writers Talking to Writers, and elsewhere. He’s also the author of There’s a Riot Goin’ On and Scars of the Soul Are Why Kids Wear Bandages When They Don’t Have Bruises. Follow MML on Twitter and Instagram. Check out some of his work for soulhead.